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Odo, Kira, DoctorBashir, ChiefO'Brien, Jadzia and Worf are in a holosuite, enjoying the performance of Vic Fontaine, the Doctor's latest holoprogram. He is singing You're Nobody 'til Somebody Loves You and everybody is enjoying themselves. After his performance, he joins the entourage where Doctor Bashir introduces him to everyone. Fontaine cracks a few jokes and uses some 20th century jargon that most of the crew don't understand. It turns out that he is a self-aware hologram and a very astute and insightful one on top of that. He is immediately able to tell that Worf and Dax have not been married for a long time and that O'Brien misses his wife. But he stops before saying anything about Kira and Odo, understanding that it is best to not talk about it for the moment. Before they leave, he advises them to dress fancy the next time for the occasion as currently they all look like a "trapeze act".

After the group leaves the holosuite, they continue on about how impressed they are with the program and Fontaine in particular. Bashir suggests meeting up again the next evening to hit the casinos and play a little blackjack and roulette after Vic's performance. While Dax is rather enthused about going back again, Kira says that she is leaving for Bajor in the morning. Dax slips and tells her to say hi to Shakaar Edon for her, before realizing that she might have said too much. Odo becomes somewhat irritated when he hears what Kira is up to. After she leaves, Bashir carries on about Fontaine, telling O'Brien that if it wasn't for his pointers, he would not be dating EnsignWalker now. He says that Fontaine knows quite a lot about life, love and women, the three things - O'Brien jokes - Bashir apparently knows nothing about. Odo, who is standing right there, hears all of this and is suddenly intrigued.

The next day, the Constable is having a conversation with Quark in his office. Quark tells him that it's been over a year since Kira broke up with Shakaar and that in all this time, Odo has done nothing about it. Odo says that it is not that simple, but for Quark it is quite simple: Odo had plenty of opportunities and he let them slip away. When Odo dismisses Quark's advice, Quark tells him that Odo is in fact not a very lovable person, as he is cold, rigid and remote. Before he leaves, however, Odo comes around and asks him for a favor: access to Dr. Bashir's new holosuite program.

The Constable returns to the holosuite to talk to Vic about his situation with Major Kira. Vic states his accurate assessment that Odo loves Kira but she considers him a friend. Vic adds that women have been known to change their minds and that it is really not that hard to get through to them, especially if they already like you. Odo says that Kira is aware of his feelings for her but that she prefers another man with great charisma. Vic replies that it is not the other man he has to worry about but himself. He asks him to lose his frozen-solid appearance and to allow those feelings he has inside of him to bubble to the surface. He tells him that if he wants to win the girl, they gotta thaw him up a little bit and that it was time they had some fun - a concept which is quite unknown to Odo and which Vic points out is precisely the problem. So a long learning process begins for Odo. He immediately changes into a tuxedo and Vic puts him behind a piano and together they perform a song that exhilarates Odo. Vic's goal is to have the Constable become less shy and more socially at ease every day so that in the end he can win over his heart's desire.

After the show, Odo and Vic are in Vic's apartment, discussing Odo's experience on stage. Odo is visibly relaxed, until he admits to Vic that he is grateful that his friends did not witness the act. Vic advises Odo to take deep breaths to relax. Odo is skeptical, but tries it. He is just beginning to enjoy this when there is a knock on the door. Vic has invited two women to his apartment to interact with Odo. One of the women admires Odo's 'artistic hands' and speaks with him about music, having seen the piano act at the club. Odo is uncomfortable with the attention, especially when the woman starts hitting on him. Vic sees his discomfort, and invites the women and Odo to a restaurant. Odo declines the invitation, being more interested in Major Kira than the holosuite woman, but Vic convinces him that he needs to practice with other women in order to pursue Major Kira.

Captain Sisko is even surprised when he first hears his Chief of Security humming a song in his office, a change he is happy to see. Sisko joins along in singing with Odo and snaps his fingers to the tune.

When Kira decides to lengthen her stay on Bajor with Shakaar, Dax and Bashir grow curious about the state of her relationship with the First Minister. Later, while traveling to Ops together in a turbolift, Dax tells Bashir that she sees through the nature of the relationship between the Constable and the Major, a fact that Bashir seems to ignore.

During another lesson in the holosuite, Odo has a little confrontation with Vic about an holographic copy of Kira (Lola Chrystal), saying that he will never be able act normally, knowing she is not the real Kira. Vic promises Odo that he will work on the hologram's personality. Later, without Odo's knowledge, Vic invites the real Kira to a date in the holosuite on the Constable's behalf.

During following dinner, Odo is really at ease with the Major, daring to show her his real personality, without knowing to whom he is really talking. In the end, we understand that the Major has genuine feelings for Odo, but the evening is spoiled when the truth is uncovered, ending with Odo storming out of the holosuite, part because he was lied to and part because he couldn't explain himself to Kira.

On the next day, Kira is talking with Dax and, after some thought (about moments of true clarity), decides to go talk to Odo about the dinner. She has to deal with Odo, more distant and cold than ever, but eventually the Major is able to reach to him. Odo asks if Kira would expect him to kiss her after a date, and Kira replies that perhaps she would. Odo then wonders aloud why they don't dispense with the pleasantries and kiss right there, to which Kira doesn't object. Suddenly, Odo grabs her and they have a first kiss right on the Promenade, to the surprise of numerous onlookers, including Dax, Quark, and Morn. Following this incident, Odo goes back in the holosuite to thank Vic about all the things he has done, even if some looked like mistakes at first.

The main reason this show was made was to finally get Odo and Kira together as a couple. That Odo had feelings for Kira had first been hinted at in the second season episode "The Collaborator". This was confirmed in the third season episode "Fascination" when Lwaxana Troi realizes it. Odo himself admitted to it four episodes later, in "Heart of Stone", albeit to the Female Changeling, who he thought was Kira. However, in the fourth season episode "Crossfire", Odo comes to accept that Kira is in love with Shakaar and so he decides to bury his feelings for her. The fifth season episode "A Simple Investigation" seemed to confirm that Odo had indeed gotten over Kira, but a few episodes later, in "Children of Time", Kira herself discovers his feelings for her, and it is revealed that he is still madly in love with her. Then, in "Call to Arms", Odo decides not to pursue her or ask her out until the current crisis was over. However, his love for her remained unabated, and it was the strength of his feelings for her that prevented him from siding with the Dominion in the episode "Sacrifice of Angels". It is at this stage in the arc where "His Way" takes place.

In terms of the writing of this episode, Ira Steven Behr explains, ""Children of Time" basically gave us the impetus to do. We'd pulled on that thread for so long without really doing anything with it, and we were running out of time. I already knew that at the end of the series Odo would be going back to the Founders to become goo. And even though I didn't know the title "What You Leave Behind" yet, I knew that Odo had to leave something behind of real value. And it just seemed to me that Kira was that value." (Star Trek: Deep Space Nine Companion)

This episode marks the first appearance of James Darren as Vic Fontaine on the series. Ira Steven Behr had been planning a character like this for several years; a Rat Pack type guy who would dispense advice on love and life to the crew of Deep Space 9. He originally tried to introduce the character during the fourth season, where he would be played by Frank Sinatra, Jr. Behr and Robert Hewitt Wolfe wrote a sample scene and casting director Ron Surma brought it to Sinatra, but he was only interested in playing an alien - he didn't want to play a human, and he certainly didn't want to play a character partly based on his own father. During the fifth season then, Behr and René Echevarria decided to introduce the character in the episode "A Simple Investigation". This time, a proper scene was written, and the character was given the name Vic Fontaine. Behr wanted Steve Lawrence to play the role, but when the first draft of the script ran long, and Lawrence proved unavailable, the scene was dropped altogether. Over the course of the following year, the role was offered to Robert Goulet, Tom Jones and Jerry Vale, all of whom turned it down. Then, Behr and his close friend Frederick Rappaport ran into James Darren at a memorabilia sale in Beverly Hills. Neither of them knew him, but Rappaport went up to him and starting chatting like they were old friends. According to Behr, "I see this guy is handling Fred so well, and is so smooth, and so friendly, and so likable, and looks so good." As such, Behr decided to offer Darren the role. The next day, Surma sent the script of "His Way" to Darren, and Darren agreed to come in for a talk, although he emphasized he wasn't going to audition or do a reading, he was just coming in for a conversation. When he came in, he began to discuss how he owns a pair of Dean Martin's shoes, and, as Behr explains, "Suddenly, he starts talking about him and Frank and Dean and gambling and making all this money, and suddenly, we realize that he's doing the part. It catches us totally by surprise. We're sitting there with the script pages and don't even realize it. He had gone right from being Jimmy to being Vic – without a beat." (Star Trek: Deep Space Nine Companion)

Neither Nana Visitor nor Rene Auberjonois wanted Kira and Odo to become romantically involved, with both of them feeling that the characters should remain just close friends. According to Visitor, "I'm not much of a fan of Odo and Kira being together, but they found a way to make it all make sense. I've always felt I have to open my mouth and pick my fights. And even though I know there's a certain amount of fights I'm going to lose, I always do it anyway. That was one I lost." (Star Trek: Deep Space Nine Companion)

Although the first take of the kiss between Odo and Kira was the one seen in the finished episode, the experience of acting in the scene was not particularly enjoyable. As Auberjonois explains, "We started the scene and when we got to the mark, boom, we kissed each other. When they yelled cut, we stopped. I looked at Nana, and her face was sort of orange, and weird, and Dean Jones, my makeup artist, looked at me and went, 'Oh God.' We had been so anxious about it we just sort of went 'Khuh,' and kissed, and my makeup got all over her face and I tore my mask! Now when people ask, 'Well, what was it like to kiss Nana?' I say, 'The definition of safe-sex is this latex mask. It was the most unsensual kiss I'd ever had. I didn't feel anything'." (Star Trek: Deep Space Nine Companion)

Nana Visitor herself chose the song "Fever" because of her mother's friendship with Doris Duke, a socialite and patron of the arts, and one of the richest women in the world. When Visitor was a child, she and her mother would visit Duke's mansion in New Jersey, and Duke would play piano and sing for them. On one particular visit, Duke sang "Fever", and the way she sang the song had a huge impact on Visitor, who was nine at the time. As Visitor explains, "She did "Fever" with this very breathy quality to her voice, and I remember thinking, 'Oh, that's a real sophisticated woman.' That was a personal connection for me. It was a memory from when I was a little girl of what I thought a woman should be like – and I got to be that woman." (Star Trek: Deep Space Nine Companion)

Of the music for this episode, Jay Chattaway explains, "We were still picking tunes on the way to the recording studio because so many of them were cleared at the last minute, I couldn't really do full arrangements of them in advance, so I only wrote generic intros and endings. I didn't know what the rhythm was going to be, or the key, but when the tune did get cleared, I'd just say, 'Okay, we're going to use intro number two,' and I would quickly rearrange it for the tune in the studio. If I would have written the music out too much, maybe it wouldn't have had the magic of a lounge band. Our musicians were improvising as if they really were combo players." (Star Trek: Deep Space Nine Companion)

This episode is a personal favorite of Ira Steven Behr, who is exceptionally proud of it; "To do a nice romantic comedy without a lot of clichés, to be clever, to not over-do it, and to have emotion rather than sentimentality, empathy rather than sentimentality, is incredibly difficult. Especially in a series like Star Trek that isn't geared to that kind of stuff." (Star Trek: Deep Space Nine Companion)

This episode was not entirely well received by some fans, something which bitterly disappointed Behr; "The quality of the show is not apparent to everyone, and that's really, really sad. Because that show is as perfect an episode as we ever did. You would be hard-pressed to find moments that don't work. It does exactly what it's supposed to. As loony as the show might seem, it's a real triumph. I'm not saying it's the only triumph by any means, but it's the one that's most masked, I guess, the one that's toughest for the audience to recognize." (Star Trek: Deep Space Nine Companion)

Behr also commented "I don't think the fans of Star Trek realize just how difficult a show like "His Way" or "Badda-Bing, Badda-Bang" is. They think that "Far Beyond the Stars", "The Visitor", a very socially conscious show or a show of a very sensitive drama, those are the shows that are the toughest to do. But in a series like this, to do light, successful humor, romance, is incredibly hard on every level. Not just the writing, but just production-wise and everything. I think part of the reason that we love them so much is because we know just what kind of sweat and blood went into them, to make them seem so fluffy, and so light and clever, whenever they are working, those qualities". (Cinefantastique, Vol. 32, No. 162 #4/5, p. 55)

This show is one of director Allan Kroeker's personal favorites; "I had a marvelous time on "His Way". It probably should be illegal to have that much fun." Ira Steven Behr says of Kroeker's involvement with this episode, "Allan has to take a lot of the responsibility for the success of the show, because he understood it, and he gave it a wonderful, wonderful, wonderful, wonderful look and feel." (Star Trek: Deep Space Nine Companion)

Rene Auberjonois commented "When I got the script for "His Way", I resisted it the first time I read it. I thought, 'oh, this is silly'. I thought that because I was so into the painful aspects of Odo, the tortured hidden love aspect of his relationship with Major Kira, I could feel myself sort of going into the place of 'my character wouldn't do that'. I then did what I always try to do. I took a deep breath and I sat down, then read the script right through again. By the time I read the script for the second time I was convinced that it was the right way to go and I really looked forward to doing it. It turned out to be one of the most enjoyable experiences I've had so far on the show". ("The Shape of Things to Come", Star Trek Monthly, issue 43)

In discussing the creation of the Lola Chrystalhologram, Vic refers to the events of "Our Man Bashir" ("Do you know how difficult it was to for me get a holographic image of Major Kira? Lucky for you, Julian used her image in one of his spy programs — though it did take me an hour to get rid of the Russian accent." — Vic to Odo). Lola's query of "who's Kira?" is reminiscent of Anastasia Komananov's questions "who is this Nerys Kira?" and "who is Dax?" This line is also a reference to "Meridian" in which Quark has extreme difficulty obtaining Kira's image in order to fulfill Tiron's request for a "personalized" holosuite program.

When Quark tells Odo that it has been over a year since Kira and Shakaar broke up, he is referring to the fifth season episode "Children of Time".

The reference to "Shecky" which confuses Odo is most likely referring to Shecky Greene, a comedian who headlined in Vegas for over 30 years. Victor Borge, the other name Odo is unfamiliar with, was a Danish comedian, musician, author and actor, who often performed in Vegas under the moniker 'The Great Dane'.

When Vic Fontaine says "I remember that weekend with Frank," there is a slight wink to the audience; actor James Darren was good friends with Frank Sinatra Jr. and he knew both Frank and Nancy Sinatra well.